Potassium Hydroxide → HCID 23312290, compound

HRID 2057421Notes

Reaction equation

HRID 2057421 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[O:16][C:15]3[CH:17]=[CH:18][C:19]4[C:24]([C:14]=3[CH:13]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)CO>[CH:13]1[C:14]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][C:15]=2[O:16][C:12]=1[CH:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54207843HCID 54207843, compound

Product 1

HCID 23312290HCID 23312290, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

7.8 g of 4-(naphtho[2,1-b]furan-2-yl)-1-piperidinecarboxylic acid ethyl ester is dissolved in 60 ml of ethylene glycol. After the addition of 40 ml of a 50% aqueous potassium hydroxide solution, the formed cloudy solution is heated, with vigorous stirring, for 15 hours at 160°. The reaction solution is thereupon cooled to 20° and extracted twice with 500 ml of ethyl acetate. The organic phases are washed five times with 1 liter of water each time, dried over sodium sulphate, filtered, and concentrated by evaporation. The residue is dissolved in 400 ml of 2 N hydrochloric acid, and the acid solution extracted with toluene. The aqueous solution is then adjusted by addition of 10% sodium hydroxide solution to have a pH value of 12, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered, and concentrated by evaporation to obtain crude 4-(naphtho[2,1-b]furan-2-yl)-piperidine. The hydrochloride is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 225°.

Workup

  1. temperaturethe formed cloudy solution is heated, with vigorous stirring, for 15 hours at 160°
  2. temperatureThe reaction solution is thereupon cooled to 20°
  3. extractionextracted twice with 500 ml of ethyl acetate
  4. washThe organic phases are washed five times with 1 liter of water each time
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. dissolutionThe residue is dissolved in 400 ml of 2 N hydrochloric acid
  9. extractionthe acid solution extracted with toluene
  10. additionThe aqueous solution is then adjusted by addition of 10% sodium hydroxide solution
  11. extractionextracted with 1 liter of chloroform
  12. dry with materialThe chloroform solution is dried with sodium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-718d7fac3bd4400cba570d2c0e62a248
Source dataset
uspto-grants-1980_07
Patent number
US04210655

Reaction notes

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